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The Uniquely Confounding Career of Curt Schilling

The onetime postseason hero was denied entry into the Baseball Hall of Fame on Tuesday, most likely not because of his résumé, but rather his recent inflammatory rhetoric. But his career remains impressive—even more so when considering how it started.

Harrison Freeman

If Curt Schilling ever enters the Baseball Hall of Fame, it won’t be because of the writers. Like his fellow faces on the Mount Rushmore of Cooperstown “character clause” concerns—Barry Bonds, Roger Clemens, and Sammy Sosa—Schilling came up short in his 10th and final year of eligibility on the BBWAA ballot. Although players often enjoy a surge of support in their last crack at Cooperstown, Schilling’s approval rating declined by 12.5 percentage points relative to the previous year, likely because of his backing of the January 6 insurrection and his (denied) request to be removed from the ballot. Thanks to his post-playing-career record of inflammatory, intolerant, and conspiratorial statements, he appeared on only 58.6 percent of ballots in his last rodeo with the writers, well short of the 75 percent needed for induction. (Only Schilling’s former teammate David Ortiz cleared that threshold this year, on his first ballot.)

Whichever metric one uses to assess Hall worthiness irrespective of character—career WAR, JAWS, Hall rating—Schilling is a top-20 or top-30 pitcher of all time, and the best pitcher other than Clemens who hasn’t been enshrined. That’s without accounting for the excellence of his 19 career postseason starts, in which he recorded a 2.23 ERA while averaging more than seven innings per outing en route to three titles and two series MVP awards. Fourteen of Schilling’s postseason games were won by his team, and he trails only Mariano Rivera in career postseason win probability added. Schilling talked and tweeted his way out of an open-and-shut Cooperstown case, though he may find favor with the members of the Hall’s Today’s Game Committee, who will weigh his credentials this December and, if necessary, in December 2024.

As a player, Schilling was prone to squabbles with teammates, management, and media members, but he also won a slew of awards for philanthropy. (The ALS Association made him and his wife the first inductees into its Hall of Fame.) His subsequent turn toward extremist rhetoric is regrettable mostly because of the misinformation and hate he’s spread. But it’s also a shame from a sports perspective, because his comments have overshadowed his career—and his career was incredible. In one respect in particular, Schilling is unique among Hall of Fame–caliber players. And that aspect of his career deserves to be remembered—and, perhaps, explained—regardless of whether his words deprive him of a plaque.

Here’s how Schilling stands out: Based on the beginning of his career, he had no business becoming an all-time-great pitcher. From 1988 through 1991, Schilling threw 145 undistinguished innings for the Orioles and Astros, recording a 4.16 ERA (88 ERA+) and a 1.6 strikeout-to-walk ratio while working almost exclusively in relief. He entered his age-25 season with 0.2 career Baseball-Reference WAR to his name, one of the lowest totals of any player who would go on to amass 70 or more WAR.

Lowest WAR Entering Age-25 Season Among Players With 70+ Career WAR

Name Career WAR WAR Through Age 24
Name Career WAR WAR Through Age 24
Gaylord Perry 90.0 -0.9
Warren Spahn 100.1 -0.6
Luke Appling 77.6 -0.5
Lefty Grove 106.8 0.0
Phil Niekro 95.9 0.0
Eddie Plank 90.9 0.0
Old Hoss Radbourn 75.4 0.0
CURT SCHILLING 79.5 0.2
Randy Johnson 101.1 0.6
Bob Gibson 89.1 0.7
Nolan Ryan 81.3 2.5
Wade Boggs 91.4 3.9
Tom Glavine 80.7 4.0
Ted Lyons 70.5 4.7
Honus Wagner 130.8 4.9

Schilling made up for his slow start by being a beast on the back end; only five pitchers have ever produced more WAR from ages 30 through 40. His failure to launch before his mid-20s is unusual, but—as evidenced by the table above—not unique. What’s unique is that Schilling was traded three times before his age-25 season started. In general, it bodes poorly for prospects when the teams that know them best decide to deal them. No other player whom three or more teams traded before his age-25 season has ever gone on to have a career in the same stratosphere as Schilling’s. In fact, Schilling nearly tripled the career WAR total of the next-best three-time trade chip. (Note: Nelson Cruz, Claudell Washington, and Jorge De La Rosa came close to qualifying for this list, but their third trades went down during their age-25 seasons.)

Highest Career WAR Among Players Traded 3+ Times Before Age-25 Season

Name Trades Career WAR
Name Trades Career WAR
CURT SCHILLING 3 79.5
Gio González 3 28.6
Jason Bay 3 24.8
Milt Stock 3 22.7
Ken Brett 3 16.3
Luis Castillo 4 14.2
Tito Francona 3 14
Jake Westbrook 3 13.1
Lou Piniella 3 12.4
Dennis Rasmussen 3 11.1

Because Schilling was moved multiple times before he began to pile up accolades, he holds another singular distinction. Schilling is the only player involved in more than one of the 15 most lopsided trades in AL/NL history, as measured by the future WAR produced by players on both sides—and he was involved in three. The table below lists those 15 trades, with the ones featuring Schilling ranking first, fourth, and 15th. (Technically, the most lopsided trade of all time was the 1899 transaction that sent 12 players, including three Hall of Famers, from the Louisville Colonels to the Pittsburgh Pirates, but because that was less a traditional trade than a transfer between two teams with the same owner, I’ve excluded it from the list.)

Most Lopsided AL/NL Trades, by Net Future WAR Produced

Date Won Lost WAR Added WAR Lost Net WAR Players Acquired Players Dealt
Date Won Lost WAR Added WAR Lost Net WAR Players Acquired Players Dealt
1/10/1991 HOU BAL 139.4 0.7 138.6 CURT SCHILLING, STEVE FINLEY, PETE HARNISCH GLENN DAVIS
12/5/1988 TEX CHC 113.5 4.6 108.9 Rafael Palmeiro, Jamie Moyer, Drew Hall Mitch Williams, Steve Wilson, Paul Kilgus, Curt Wilkerson
12/15/1900 NYG CIN 106.5 -0.7 107.2 Christy Matthewson Amos Rusie
7/29/1988 BAL BOS 114.2 13.9 100.3 CURT SCHILLING, BRADY ANDERSON MIKE BODDICKER
1/20/1965 CHW CLE/KCA 92.3 0.9 88.8 Tommy John, Tommie Agee, John Romano Fred Talbot, Jim Landis, Cam Carreon, Mike Hershberger
4/21/1966 CHC PHI 97.2 10.8 86.4 Fergie Jenkins, Adolfo Phillips, John Herrnstein Larry Jackson, Bob Buhl
12/9/1982 TOR NYY 84.3 -0.7 85.0 Fred McGriff, Mike Morgan, Dave Collins Tom Dodd, Dale Murray
12/10/1971 CAL NYM 85.4 2.8 82.6 Nolan Ryan, Leroy Stanton, Frank Estrada, Don Rose Jim Fregosi
11/29/1971 CIN HOU 95.1 14.8 80.3 Joe Morgan, César Gerónimo, Dennis Menke, Jack Billingham, Ed Armbrister Lee May, Tommy Helms, Jimmy Stewart
1/8/2001 OAK KCR/TBD 82.4 3.2 79.2 Johnny Damon, Mark Ellis, Cory Lidle Ben Grieve, Ángel Berroa, AJ Hinch
5/25/1989 SEA MON 108.5 30.9 78.0 Randy Johnson, Brian Holman, Gene Harris Mark Langston, Mike Campbell
7/29/1989 CHW TEX 95.3 17.5 77.8 Sammy Sosa, Wilson Álvarez, Scott Fletcher Harold Baines, Fred Manrique
6/27/2002 CLE MON 99.7 22.5 77.2 Cliff Lee, Brandon Phillips, Grady Sizemore, Lee Stevens Bartolo Colon, Tim Drew
8/30/1990 HOU BOS 79.9 3.9 76.0 Jeff Bagwell Larry Andersen
4/2/1992 PHI HOU 79.3 4.7 74.5 CURT SCHILLING JASON GRIMSLEY

Before Schilling established himself as a frontline starter for the Phillies in 1992, the Red Sox, Orioles, and Astros all opted to trade him. Each of those teams made what in retrospect seems like a master stroke in acquiring him—and each of those teams, after an interlude of no longer than two and a half years, made what in retrospect looks like a huge blunder in dealing him away. How was it that between July 1988 and April 1992, three different teams gave up on Schilling, or at least decided to part with him in exchange for returns that seem meager in hindsight? By interviewing the architects of those trades and reviewing contemporary coverage, we can unravel the mystery of how a young journeyman matured into an old ace—and identify a few lessons for any GMs who hope to avoid ending up on the wrong end of a future fleecing. Let’s tackle these notorious trades one by one, in chronological order.

July 29, 1988: Boston trades Schilling and Brady Anderson to Baltimore for Mike Boddicker (net WAR gap: 100.3)

Dave Holt, manager of the 1988 New Britain Red Sox, remembers the moment a few days before the big league trade deadline when he learned he was losing his Double-A ace. The minor league team was in the midst of a stretch of doubleheaders, and Schilling was scheduled to start the day’s second game. “They came running out of the front office, like between games or just at the end of the first game,” he says. “And they said, ‘Hold him out, hold him out. There’s something brewing.’”

That something was a landmark deadline deal. Holt had managed Anderson in the minors, too, and he knew that they were “untouchable-type guys … that had major league written all over them.” Watching the Sox send both to Baltimore, he says, “threw me for a loop.”

The Red Sox had selected the 19-year-old Schilling out of Arizona’s Yavapai College in the second round of the 1986 January draft—an inspired pick, considering Schilling would surpass the combined career WAR totals of the 38 players who were drafted ahead of him. He was signed by scout Ray Boone, who had him high on his draft list. “With his ability and with his size, he was kind of a no-brainer in our mind to take,” says Ed Kenney Jr., a Red Sox player development and scouting assistant in 1986 who ascended to farm director in ’87.

Although it would be years before the right-hander made Boone look brilliant, Schilling looked the part of a power pitching prospect early on. He posted a 2.59 ERA in his Low-A pro debut, struck out more than a batter per inning in A ball in ’87, and managed a 2.97 ERA in 21 games and 17 starts in Double-A prior to the ’88 trade deadline. “To be drafted in ’86 out of high school and pitching pretty successfully in Double-A in ’88, he was on a pretty good track to become the pitcher that he became,” Kenney says. “That’s a fast track, and then he stalled.”

The Sox didn’t dump the 21-year-old Schilling because of a problem personality. Holt, who says Schilling’s stuff compared favorably to that of former Red Sox top prospect Clemens, remembers him as an amiable, coachable, and confident kid who tended to horse around rather than focus on preparation and training between starts. “He was not quite as mature and just not as professional as the other guys at that time,” Holt says, adding, “He wasn’t polished off the field. He wasn’t polished in his work ethic and just hadn’t quite grown up yet.” As Kenney puts it, “He always had the arm, and he always had the build and the strength and the talent. He didn’t always have the maturity level that it takes to put all that together.” Holt’s report on Schilling in 1988 noted that he “pitches young and he acts young” and called him “a bull in a china closet” who “gets out of sync easily.” But it also said that “he wants the ball and he wants to be a successful pitcher,” and that while “it might take some time,” he “should be a good pitcher.”

The 24-year-old Anderson, meanwhile, had entered the season as Boston’s top prospect, per Baseball America—which didn’t put Schilling in the top 10—and he’d made his major league debut as the team’s leadoff batter and center fielder on Opening Day. Anderson struggled offensively as he worked on some swing changes and was demoted to Triple-A, but he was the headliner on the prospect side of the swap. Red Sox GM Lou Gorman—who had attempted to trade Anderson and four other players for Cal Ripken Jr. earlier that year—reportedly tried to get Orioles GM Roland Hemond to accept 25-year-old outfielder and first baseman Todd Benzinger in the Boddicker deal (which Gorman disputed). But Baltimore insisted on Anderson—wisely, as it turned out, because Benzinger would be a career sub-replacement-level player. Between Benzinger, the even younger Ellis Burks, Mike Greenwell, and Carlos Quintana, and the old-but-still-solid Dwight Evans, the Sox were stacked enough in the outfield to reluctantly let Anderson go.

The O’s also pushed for Schilling. “Boston didn’t want to give him up either,” says Doug Melvin, who was then the Orioles’ farm director. Melvin continues, “We had a scout named Leo Labossiere, and he kept telling Roland, ‘You got to make this deal, but you got to get Curt Schilling put in.’ … And Roland just kept hounding Lou Gorman about [how he’d] do the deal, but he had to have Schilling.”

Labossiere had been Hemond’s high school baseball coach, and as Hemond’s career in the sport flourished, he hired Labossiere wherever he went. The late Labossiere’s son Dave—the longtime Astros trainer who heroically tweezed a moth out of Astros outfielder Mike Simms’s ear—says the Labossieres lived in Rhode Island, and that Leo was assigned to scout the Sox affiliates in Pawtucket and New Britain. “My suspicion is that my father saw [Schilling] in New Britain and liked his arm and said, ‘Well, if you can get him in as a throw-in, do it,’” Dave says.

The Orioles, who had infamously started the season 0-21 and were bound for baseball’s worst record, were in prime position to extract their top targets, because the Boston rotation had a Boddicker-shaped hole. “We were in the pennant race and needed an arm,” Holt says. On the morning of July 29, the Red Sox sat in third place in the AL East, half a game behind the Yankees and 2 1/2 back of the Tigers. Red Sox starter Oil Can Boyd had just suffered a shoulder injury that would cost him most of the rest of the season, and the 30-year-old Boddicker—the last pitcher remaining from the Orioles’ ’83 championship staff—was averaging seven league-average innings per start. “This guy could mean the difference for us,” Red Sox manager Joe Morgan said.

In fact, Boddicker did. He raised his game down the stretch, pitching to a 2.63 ERA over 89 innings as the Sox edged out Detroit to take the AL East title by a single game. Boddicker bombed in the third game of the ALCS as the A’s swept the Sox, but one can see why the Sox were willing to part with two top prospects in hopes of ending their 70-year title drought and easing the sting of ’86. Nor was the righty a pure rental: Gorman signed the impending free agent to a two-year extension as a condition of the deal, and Boddicker helped propel the team back to the playoffs in 1990, only for Oakland to sweep the Sox again.

Of all the lopsided Schilling trades, this one is the most excusable, and the one that could most plausibly still happen in 2022—though it would be tough to pry two team-controlled talents away from one of today’s prospect-prizing front offices in exchange for a modern-day Boddicker. “It wasn’t a case of us not knowing that we had two pretty good prospects,” Kenney says. “We saw them as two guys that could go on to be an everyday center fielder in the big leagues and a starting pitcher, as they both did. But … you don’t get a chance to go to a World Series every year, and you have to sometimes bite the bullet.” Boston’s next pennant wouldn’t actually arrive until 2004, when Schilling, whose career had come full circle, would sport a bloody sock as he helped pitch the Sox to their first title since 1918. Three years later, the 40-year-old would win a World Series game in his final start, which assisted the Sox in securing another Series sweep and earned Schilling a spot in the Red Sox Hall of Fame.

Shortly before the ’88 trade was made, the New Britain Red Sox ran a morning summer camp for kids, and Schilling was one of Holt’s helpers. “I gave him a little stipend for helping us out,’ Holt says, “and just before he left, the last thing I think I remember him saying was, ‘Hey, Holtie, do you have any of that money for that camp yet?’ He didn’t want to leave town without his camp money.”

Schilling wouldn’t have to sweat stipends for long. He continued to pitch well for the O’s at Double-A Charlotte, and the big club called him up to make his major league debut on September 7 against his old organization, the Red Sox. As Evening Sun Orioles beat writer Ken Rosenthal reported, the sleep-deprived pitcher, who had skipped Triple-A, repeatedly mixed up catcher Mickey Tettleton’s signs, but Schilling held the Sox to three runs over seven innings. The first of his 3,116 strikeouts—15th most all time—came at Benzinger’s expense. “I can see why we were reluctant to give him up,” Sox skipper Morgan said.

January 10, 1991: Baltimore trades Schilling, Steve Finley, and Pete Harnisch to Houston for Glenn Davis (net WAR gap: 138.6)

Woof. The Glenn Davis deal, as it would have been described when it was completed 31 years ago this month, is the most lopsided trade of all time. Not only did each of the three youngsters in the trade go on to dwarf Davis’s WAR from January ’91 on, but each of them easily outproduced Davis during the veteran’s three seasons with the Orioles (which would be the last of his big league career). Finley and Harnisch combined to produce nearly 20 times the WAR that Davis did in 1991 alone. On second thought, “woof” was an understatement.

In fairness to the Orioles, Davis had been one of baseball’s best hitters in the years leading up to the trade: He finished in the top eight in NL MVP voting in 1986, ’88, and ’89, hit 30 or more homers in each of those years despite the power-suppressing effects of the Astrodome, and ranked 12th in OPS+ among all major leaguers with at least 1,500 plate appearances from ’88 through 1990. “We were looking for a cleanup hitter, a guy to hit in the middle of the order behind Cal Ripken, and Glenn Davis was the guy we identified,” Melvin says. “Houston would trade him for younger players, and he would’ve fit right in the lineup with Baltimore.”

Would’ve, that is, if he’d kept hitting the way he had in Houston. But when the Orioles acquired him, Davis was about to turn 30, and unbeknownst to Baltimore, almost all his value lay behind him. He soon suffered an unusual nerve injury in his neck and later broke his jaw in a bar fight and got hit in the head in the dugout by a foul ball, all of which sapped his power and culminated in the Orioles releasing him in September 1993 following an argument over playing time with manager Johnny Oates.

Not that the Astros knew that Davis was about to break. “As the local media called it, we were running a fire sale,” says former Astros GM Bill Wood, who had been promoted to the job in December 1987. “We were actually doing what the media nowadays calls tanking, which was trying to build for the future with players with promise.” The Astros had won the NL West in 1986, and they’d tried and failed to run it back for a few years before concluding in 1990 that it was time to start over. The fire sale started during the season, as the Astros sent Larry Andersen, Bill Doran, and Dan Schatzeder to contending teams. One of those trades paid dividends, as the Red Sox, locked in another tight playoff race two years after the Boddicker deal, made another one of the most lopsided swaps ever. Astros scouts Tom Mooney and Stan Benjamin, who had covered Jeff Bagwell in Boston’s system, “kept saying, ‘Try to get Bagwell, try to get Bagwell,’” Wood recalls. “And we just kept holding out for Bagwell. And right at the last minute … they needed [Andersen] for the postseason, and they made the deal.”

Davis was one of the most appealing players remaining on the Astros’ roster, and the Orioles were the most aggressive suitor. The trade took months to complete, with talks kindling in the fall and continuing into the GM meetings, the winter meetings, and the holidays. “We had scouts that covered Baltimore and felt like Finley was going to be able to hit left-hand pitching,” Wood says. “We liked Harnisch as a potential starter for the future. And the young prospect in the group was Schilling, who we liked very much from the standpoint of his tools, which if he could put them together, he could be a positive addition.”

When the Sox had parted with Brady Anderson, they had been dealing from depth. The Orioles were also. “The Orioles were very strong with center fielders,” Melvin says. “We had Mike Devereaux, Brady Anderson, and Steve Finley. And I know Roland, in discussion, we said, ‘We can afford to give up one of the center fielders.’ Houston was on Finley. They did like Steve the whole time. … I don’t think anybody saw him having the power that he did later.”

The O’s were rich in pitching prospects, too. In the spring of 1990, Schilling had been Baseball America’s no. 2 Orioles prospect behind Ben McDonald, the second-ranked prospect in the sport. In addition to McDonald, the 1991 O’s staff would feature rookies Arthur Rhodes and Mike Mussina, who entered that season as the no. 6 and no. 19 prospects in baseball, respectively. The Astros were asking for two pitchers in return for Davis, and the Orioles offered Bob Milacki and Jeff Ballard. But “they went for the two big arms,” Melvin says. “Milacki and Ballard were not power-type pitchers. They were sinker-ballers. And Bill Wood went for the two power arms in Harnisch and Schilling.” It helped that Houston pitching coach Bob Cluck had put in a plug for Schilling based on a recommendation from a figure from Schilling’s past, Cluck’s friend Ray Boone.

Schilling, Melvin says, “didn’t have any major problems with us in Baltimore, that we’d say, ‘Hey, we got a troubled player here. We’re getting rid of him.’” He was used with some success as a setup man in 1990, and although he started in Triple-A, the team thought it would take time to transition him to the rotation in the majors. “You can go back and look at all the quality pitchers, the Pedro Martínezes, that get traded,” Melvin says. “And teams look back and say, ‘Maybe one more year of patience would’ve been better.’”

Hemond, who died last month, was a wheeler and dealer: After he was hired in November ’87, he made 17 trades in his first 17 months with the Orioles, a total that rose to 28 by the start of the ’91 season. The problem with this trade was twofold. For one thing, the Orioles had won only one game more than the Astros in 1990; they weren’t one player away. For another, Davis (let alone another offensive reinforcement, ancient free agent signee Dwight Evans) wasn’t a dependable long-term cornerstone; Davis had missed time with a rib injury in 1990, and as he exited his 20s, with one year remaining on his contract and limited skills beyond his bat, he was overvalued in 2022 terms. “It’s just one of those deals where you just have to decide, is this what you want to do?” Melvin says. “And this is what it [was] going to cost to get an All-Star player like Glenn Davis, was two pitchers who had not established themselves yet, but they were going to be successful. … We really didn’t want to give them up.”

Although Orioles manager Frank Robinson lamented the loss of Schilling, the Orioles’ end of the trade drew raves both in Baltimore and around the rest of the game. “The Orioles made a terrific trade yesterday,” The Baltimore Sun’s John Eisenberg rhapsodized about the worst trade of all time, praising “a good piece of baseball business” that couldn’t go wrong unless Davis didn’t re-sign. “We’re a better team than we were yesterday,” Robinson said. Even that turned out not to be true; the O’s backslid to 67 wins in 1991, and although they won the sixth-most games in the majors over the following five years, they failed to finish first in their division during those years, as Finley, Schilling, and Harnisch combined for roughly 40 WAR for other teams.

April 2, 1992: Houston trades Schilling to Philadelphia for Jason Grimsley (net WAR gap: 74.5)

“This is my fourth team and I’m just 25,” Schilling told The Philadelphia Inquirer shortly after this swap. “Everyone says, ‘He’s got a great arm, but …’ I’m hoping to end that talk and make this a lopsided trade.” Did he ever. Net WAR–wise, this is the least terrible of the trio of trades, in that it was a one-for-one as opposed to a package featuring multiple players who panned out. But it may be the most embarrassing, both because the player traded for Schilling was the least accomplished to that point and because it became clear almost immediately that just as the Astros had highway-robbed Baltimore, the Phillies had swindled the ’Stros. A year after the O’s jettisoned Schilling for squat, Wood says, “We wound up doing the same thing, basically, almost giving him away. … Win one, lose one.”

In part, the Schilling trade came about because of one of the bugaboos of baseball operations executives: an antsy owner. When the Astros bottomed out 20 years later, Astros owner Jim Crane gave his front office ample time to build back up. But his predecessor John McMullen tired of defeat after the ’91 Astros’ 97-loss season.

“I was trying to put pieces in place to win for the future,” Wood says. “And that meant to me to be a contending team over multiple years. So I was trying to keep our owner away from our staff, because I knew what would happen if he got them together. And sure enough, about the end of spring training he called everybody together, and he said, ‘Bill, I know what you’re doing. I want to talk to [manager] Art [Howe] and the coaches.’ He told the guys, ‘Enough of this losing crap. We’re going all out to win.’” On the eve of Opening Day in 1992, Schilling was out of minor league options and coming off a rough spring in which he’d suffered from tendinitis. Those factors, coupled with McMullen’s win-now mandate, made Schilling the odd man out on the Astros’ young staff, and with little chance to sneak him through waivers, the trade was made.

Schilling’s third departure, like his first two, wasn’t a case of wearing out his welcome. Labossiere says he still “had an immaturity about him,” but Wood says, “I don’t remember Schilling being a difficult person,” and Cluck calls him “one of my favorites ever.” Schilling had pitched out of the pen in ’91, and though he’d struck out almost a batter per inning, he’d also walked one roughly every other inning. “He was our closer for a while, and I think that was probably a mistake … because he continued to overthrow,” Cluck says. Schilling’s .344 BABIP—which was tied for the NL high—hid his more impressive peripherals, but nobody was talking about BABIP in the early 1990s.

Through 1991, the 24-year-old Grimsley’s career surface stats were similar to Schilling’s (though Grimsley had worked exclusively as a starter), and because he’d been drafted by a previous regime, Phillies GM Lee Thomas had no personal attachment to him. “The people I relied on for assessment all agreed with me that Grimsley was a young pitcher who could be traded and hopefully get us someone who had a more promising arm,” Thomas says. In surrendering that arm, Wood went against his gut. “I found that anytime I violated my principles, I made a mistake,” he says. “And as a baseball principle, I believed in Curt Schilling because of his tools.”

Wood authored some of the sport’s most celebrated and ill-advised decisions: He made out like a bandit in the Davis and Andersen deals, but he also traded Schilling for a future reliever/bat thief who never pitched for the Astros, and he failed to draft Derek Jeter with the ’92 no. 1 pick (another byproduct of the team’s premature all-in approach). “I’m also the genius that traded Kenny Lofton,” Wood says, referring to the December ’91 exchange in which he traded Lofton (who was blocked by Finley) to Cleveland for Ed Taubensee to fill a vacancy at catcher created by Craig Biggio’s switch to second base.

“Sometimes there are moves that it takes a lot of years to forget,” Wood says. Thirty-plus years may not be enough. Whenever Wood hears Schilling’s name now, he confesses, “In the back of my mind, I’m saying to myself, ‘Self, you idiot. That’s one guy you should have held on to. Maybe you would have lasted in Houston for five more years than you did.’” Had the mid-’90s Astros had Schilling and Lofton, Wood jokes, “they might have actually beaten the Braves once in a while.”

By their own admission, the Phillies didn’t know what they had. “Some of it is luck,” Thomas says. “Some of it is in the random time when a player turns a corner and becomes the best version of the player he is meant to be. … I wasn’t smarter than anyone else. It was a combination of factors that brought out the talent.”

One factor was opportunity. Schilling started the ’92 season back in the bullpen. “His starting pitching mode had not kicked in yet, or teams didn’t recognize it,” Melvin says, adding, “And then sometimes … somebody gets injured and all of a sudden, ‘Let’s give this guy a shot.’” Injuries opened a starting slot on May 19. Schilling seized it, delighted in dominating the Astros in his first and third turns, and never relinquished the role.

But the foremost factor was the influence of Phillies manager Jim Fregosi—a man familiar with historically lopsided trades—and pitching coach Johnny Podres. Both believed in Schilling’s live arm: As Fregosi said days after the trade, “Schilling has closer stuff. He also has starter stuff.” But Podres, a multi-time champion and postseason hero himself, was the key to his transformation. “Podres did for him what I couldn’t do, and that was to get him to stop trying to throw so hard and command his fastball,” Cluck says.

That wasn’t all Podres did. Encountering the right coach at the right time could be crucial, especially in an era before ball/body-tracking tech and high-speed cameras made more systematic, data-driven player development possible; Bagwell had hit four homers as a 22-year-old in Double-A, but Houston hitting coach Rudy Jaramillo helped him turn his topspin into backspin and unleash the long balls. Podres, as was his wont, taught Schilling a changeup, and he also overhauled his curveball and advised him to replace his sinker with a four-seamer. Under Podres’s tutelage, Schilling committed to the psychological and physical preparation he’d given short shrift before. He had “gone from being a guy with above-average stuff and a marginal mind to a guy with above-average stuff who’s a thinking pitcher,” and his new idea of fun wasn’t to “go to the pub after a game and hang out with the boys,” but to remain on the mound in the ninth inning of big games.

Coaching shortcomings, overrated rosters, overvaluing of veterans, underappreciation of prospects, ownership pressure, bad batted-ball luck, and unfortunate timing: All of the above contributed to a late-blooming ace’s itinerant origins. Asked in June of ’92 whether joining the Phillies was like getting a second life, Schilling said, “It’s a first life.” By 1993, he was preaching the gospel of Podres and crediting the coach with an impact on his life second only to his dad’s.

Schilling was the winningest pitcher on the Phillies’ staff in ’92—which he acknowledged would have seemed laughable before the season—but the path to his peak wasn’t direct. Schilling lost focus for part of ’93, underwent elbow surgery in ’94, and tore his labrum in ’95. It wasn’t until 1997 that he had his first fully healthy, huge year, which his pitching coach that season, Galen Cisco, attributes to his use of video to study hitters, his willingness to pitch inside, and his consistency in spotting unhittable heaters down and away. Schilling’s career overlapped with those of four horsemen of the pitching apocalypse—Clemens, Greg Maddux, Randy Johnson, and Martínez (not to mention Mussina)—but Cisco, whose ’93 Blue Jays wound up on the wrong end of a World Series shutout, says, “In a situation where you had to win one game, he would probably be my pick.”

Schilling arguably had his best years with the Diamondbacks, but just before his statements made him a pitcher non grata, he slipped into the Phillies Wall of Fame. The 55-year-old belongs to at least four halls/walls of fame—he’s also in Arizona’s Sports Hall—and if he can keep quiet (fat chance) or find a forgiving audience on the Today’s Game Committee, he may yet enter another. He’s already defied longer odds. After all, plenty of people with questionable characters have plaques in Cooperstown. Only one 25-year-old who’d been traded three times blossomed into one of baseball’s best players ever.

Thanks to Dan Hirsch of Baseball-Reference, Debbie Nocito of the Phillies, Cassidy Lent of the Baseball Hall of Fame, and “The Batguy” of Astros Country for research assistance.

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